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Issue 44, 2014
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Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

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Abstract

Isothiourea HBTM-2.1 catalyses the Michael addition–lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl3 ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95 : 5 dr and >99% ee). Sequential addition of two different nucleophiles to a dihydropyranone gives the corresponding differentially substituted diacid derivative.

Graphical abstract: Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

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Article information


Submitted
21 Aug 2014
Accepted
23 Sep 2014
First published
06 Oct 2014

Org. Biomol. Chem., 2014,12, 9016-9027
Article type
Paper

Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

L. C. Morrill, D. G. Stark, J. E. Taylor, S. R. Smith, J. A. Squires, A. C. A. D'Hollander, C. Simal, P. Shapland, T. J. C. O'Riordan and A. D. Smith, Org. Biomol. Chem., 2014, 12, 9016
DOI: 10.1039/C4OB01788A

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